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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-14 00:50:13 UTC
Update Date2020-02-26 21:25:12 UTC
HMDB IDHMDB0004699
Secondary Accession Numbers
  • HMDB04699
Metabolite Identification
Common Name8(S)-HPETE
Description8(S)-HPETE, also known as 8-HPETE, belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Thus, 8(S)-hpete is considered to be an eicosanoid lipid molecule. 8(S)-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752312
Synonyms
ValueSource
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyeicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyeicosa-5,9,11,14-tetraenoateGenerator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyicosa-5,9,11,14-tetraenoateGenerator
8-HPETEHMDB
8-Hydroperoxyeicosatetraenoic acidHMDB
8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoateHMDB
8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoic acidHMDB
8S-HpETEHMDB
8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoateHMDB
8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid
Traditional Name8S-HpETE
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OO
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1
InChI KeyQQUFCXFFOZDXLA-VYOQERLCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroperoxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroperoxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.91ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m³·mol⁻¹ChemAxon
Polarizability39.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lxx-8191000000-f40887afa4336a868504Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9155000000-e96fa4ff2ceea124c320Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129000000-8ca36286a5e0a67d34cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-5895000000-74183959cbae04641d81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-9730000000-251dda1c693004c0368cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-20280b5caa4db081c46eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1659000000-31c2ae506e12aab615b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9640000000-dccb96b68f4a42b91f86Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023412
KNApSAcK IDNot Available
Chemspider ID7827803
KEGG Compound IDC14823
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9548880
PDB IDNot Available
ChEBI ID34487
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jisaka M, Iwanaga C, Takahashi N, Goto T, Kawada T, Yamamoto T, Ikeda I, Nishimura K, Nagaya T, Fushiki T, Yokota K: Double dioxygenation by mouse 8S-lipoxygenase: specific formation of a potent peroxisome proliferator-activated receptor alpha agonist. Biochem Biophys Res Commun. 2005 Dec 9;338(1):136-43. Epub 2005 Aug 15. [PubMed:16112079 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
Gene Name:
ALOX15B
Uniprot ID:
O15296
Molecular weight:
72522.25
Reactions
Arachidonic acid + Oxygen → 8(S)-HPETEdetails